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There are 2 daily trains from Kissimmee to Chicago. Traveling by train from Kissimmee to Chicago usually takes around 45 hours and 26 minutes, but the fastest Amtrak train can make the trip in 44 hours and 49 minutes.
|Distance||1002 mi (1612 km)|
|Fastest train||44h 49m|
|Most frequent service||Amtrak|
Which train should you take from Kissimmee to Chicago?
Amtrak is the one and only train line which connects Kissimmee, Florida to Chicago, Illinois. The schedule is relatively limited as the train only runs twice a day.
|Train||Daily Trips||Avg. Time||Avg. Price|
|Amtrak||2||1d 21h 26m||$411.77|
Amtrak is the largest passenger railroad service in America, offering daily intercity trains to hundreds of destinations across the contiguous United States, as well as several cities in Canada. Every Amtrak train comes equipped with comfortable seats with extra legroom, as well as several four-seat areas with tables in the middle. In addition, each car has a freshly cleaned restroom, free WiFi and power outlets at every seat. There are also snack bars where you can purchase drinks or food during your journey. On average, there are 2 Amtrak trains from Kissimmee to Chicago every day, as well as 1 trips on the weekends, with prices starting from $218.
Frequently Asked Questions
Is it safe to travel by train from Kissimmee to Chicago during the COVID-19 pandemic?
Our train partners have implemented several different policies to keep you safe during the COVID-19 pandemic. From limiting vehicle capacity to enhancing cleaning protocols and upgrading air filters, train carriers are committed to maintaining a safe environment. For details on what each company is doing to ensure their fleet remains safe for travel, click here.
In addition, federal law requires all train passengers to wear a face covering for the entire duration of the trip. Please make sure you are wearing a face mask or you may not be allowed to board the train.
Please visit our COVID-19 Travel Guide for more information on all carrier policies and the latest travel advisories issued by every U.S. state, Canadian province, and European country.
How long is the train journey from Kissimmee to Chicago?
The distance between Kissimmee and Chicago is approximately 1002 miles, or 1612 kilometers. The average train journey between these two cities takes 45 hours and 26 minutes, although the absolute fastest you could get there is 44 hours and 49 minutes.
Looking for ways to pass the time? Most trains are equipped with Wi-Fi, which means you can stream music, browse social media or get some work done during your ride. That said, in case your train has a spotty signal, or is among the few without Wi-Fi, we also recommend downloading TV shows and movies to your mobile device in advance of your trip. That way the ride will fly by whatever the Wi-Fi situation.
When are trains the most crowded?
Trains from Kissimmee to Chicago are the most crowded on Wednesday. Tickets also tend to be more expensive then. If you are looking for a great deal on your train tickets or just want extra room to stretch out, consider traveling on Monday instead, as it tends to be the least crowded day of the week.
When are the first and last trains of the day?
The earliest train departs Kissimmee at 12:00pm while the last train of the day leaves at 12:00pm. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.
Is there a direct train from Kissimmee to Chicago?
Trains leave the station in Kissimmee twice a day, so there are a couple of options depending on your preferred travel time. However, there are no direct trains. This means that you will need to disembark from your original train and board a connecting train at some point during your journey. You will need to remember to bring your carry-on luggage with you when you change trains. Depending on the carrier's policy, you may also be responsible for transferring your own checked baggage.
Known for its innovative architecture, cultural contributions to jazz and house music, and of course that irresistible deep-dish pizza, the many sights and experiences in Chicago make it one of the best urban vacation destinations for millennials.
You can't beat the views of the city and Lake Michigan from the SkyDeck in the Willis Tower; at over 1,300 feet, this is the highest observation deck in the U.S. Snap that classic selfie with the Bean in Millennium Park, then wander the many museums in nearby Grant Park. Navy Pier is a popular tourist hotspot for its parks, restaurants, and attractions right on Lake Michigan, and baseball fans will find paradise in Wrigleyville, home to the Chicago Cubs' Wrigley Field and sports bars galore.
Chicago's enormous parks offer plentiful opportunities for outdoor activities in gorgeous urban settings. Many companies offer kayak rentals or boat tours on the Chicago River, with special tours running on Saint Patrick's Day, when the entire river is dyed green. When you’re ready to buy some souvenirs from your epic trip, hit the big brand stores on the Magnificent Mile, or shop local in neighborhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theater, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.
Chicago is one of the biggest transportation hubs in the Midwest, and provides easy access to nearby destinations ideal for day trips, as well as international travel from two airports. Thanks to plenty of bus and train stations throughout the city, getting to the Windy City is a breeze.
Where is the train station in Kissimmee?
There is one train station in Kissimmee.
Where is the train station in Chicago?
The historic Chicago Union Station is the United States' third busiest train station and a hub for 15 Amtrak train lines with destinations throughout the country. The station also serves bus carriers like Greyhound, Indian Trails and Jefferson Lines, and offers connections to Metra commuter lines. Union Station is also just a quick walk to the nearest Chicago L lines. The current station was built in 1925, to replace the original one dating back to 1881, and today wows visitors with its impressive facade, massive columns, and opulent Great Hall. Located right in downtown and adjacent to the Chicago Loop, Union Station is equipped with many services and amenities, including phone charging stations, shops, and various food and drink options.
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